title: Intramolecular cyclization of in situ generated adducts formed between thioamide dianions and thioformamides leading to generation of 5-amino-2-thiazolines and 5-aminothiazoles, and their fluorescence properties.
abstract: Reactions of thioamide dianions, derived from secondary N-arylmethyl thioamides using BuLi, with thioformamides followed by the addition of iodine to yield 5-amino-2-thiazolines are described. Treatment of the 5-amino-2-thiazolines with iodine leads to a highly efficient production of 5-aminothiazoles. When N,N-diarylthioformamides are employed in this process, fluorescent 5-N,N-diarylthiazoles are obtained.
authors.affiliation: Department of Chemistry, Faculty of Engineering, Gifu University, Yanagido, Gifu 501-1193, Japan.
authors.forename: Toshiaki
authors.initials: T
authors.lastname: Murai
authors.forename: Fumihiko
authors.initials: F
authors.lastname: Hori
authors.forename: Toshifumi
authors.initials: T
authors.lastname: Maruyama
mesh_terms: D000588:Amines / Q000737:chemistry*; D000838:Anions / Q000737:chemistry; D003500:Cyclization; D005456:Fluorescent Dyes / Q000138:chemical synthesis*; D005559:Formamides / Q000138:chemical synthesis*; D008958:Models, Molecular; D015394:Molecular Structure; D010084:Oxidation-Reduction; D013844:Thiazoles / Q000138:chemical synthesis*; D013854:Thioamides / Q000138:chemical synthesis*
chemical_list: D000588:Amines; D000838:Anions; D005456:Fluorescent Dyes; D005559:Formamides; D013844:Thiazoles; D013854:Thioamides; C009463:thioformamide